An unexpected career in accounting

Accountant & Bookkeeper Stories

5 min read

A career in accounting can start unexpectedly. Read how musician Blake Oliver discovered accounting and co-founded a cloud integration firm.

A career in accounting can sometimes start unexpectedly. Blake Oliver was a talented cellist working as a music store manager when he discovered an interest in bookkeeping. Together with school friend Maria Sentic, Blake co-founded Cloudsourced Accounting, a bookkeeping and cloud integration firm that helps transition small businesses to the cloud.

Blake sold Cloudsourced in 2015, and now runs his own independent information resource, blakeoliver.com, where he offers small business owners and freelancers advice on accounting, bookkeeping and how to use cloud accounting software. But despite Blake’s success in the world of accounting, he insists he’s still a musician at heart.

An early love of music shaping a mind for business

Blake didn’t always plan for a career in accounting. He excelled at playing the cello from an early age, and dreamed of being in an orchestra. Blake grew up in Sacramento, and commuted to San Francisco on weekends to participate in the youth symphony.

When Blake headed off to college at Northwestern University, he entered as an undeclared major. He devoted his freshman year to exploring his options, including math, political science, Chinese, and literature.

Blake also wanted to continue with cello, as the university has one of the top music programs in the nation. However the cello teacher wouldn't work with a student who wasn't fully committed to his instrument. "You have to go all in with one thing – that's what my cello teacher taught me," Blake said. "You have no idea whether you’re going to succeed or fail – but there's only one way to find out."

Blake decided to take the plunge and auditioned for the music program that spring. He was accepted. For the next four years, Blake developed his cello performance skills alongside other elite musicians. He believes the experience helped shape him into the entrepreneur he is today.

“There are plenty of books out there about how sports can make you better at business. I think music is similar. All the lessons you learn apply to business too, from self discipline to focus to grit,” he says.

Before blakeoliver.com
Manager of a music store, CEO of Cloudsourced Accounting

Hobbies
Playing cello, spending time with his family

The “ah-ha” moment of discovering accounting

After college, Blake moved to Florida with his future wife, Samantha. He was still playing the cello but made a living managing a music store. He also worked as an office manager for a tutoring company. It was in these jobs that he was first introduced to the idea of a career in accounting.

The “ah-ha” moment occurred when he noticed inefficiencies in the tutoring company’s invoicing process. Each tutor would send paper invoices to the company, then the company would mistakenly bill the client a second time. All of this was done on paper. Blake streamlined the process by making it digital, making it much faster and more accurate. “We reduced errors dramatically,” Blake recalls. “I was hooked after that.”

From freelance bookkeeping to an accounting career

Soon after discovering his knack for bookkeeping, Blake and his wife moved to Los Angeles. He planned on working toward his CPA license at night and freelancing as a bookkeeper during the day. However, he soon discovered he could make a good hourly rate even without a CPA qualification. So he put his studies on hold and focused on building his career in accounting.

Tackling the problem of inefficiency

It didn’t take Blake long to see there had to be a better way to do accounting. Much of his day was spent in Los Angeles traffic, driving between client offices. This was preventing him from taking on additional clients and increasing revenue. It was a hurdle that needed to be overcome in order for his business to recognise its full potential.

Around the same time, Blake reconnected with college friend and fellow accountant, Maria Sentic. The two launched Cloudsourced Accounting with the goal that their practice would operate using cloud technology.

“Having an equal business partner to lean on is crucial,” Blake says. “I could never have made it through these first two years without Maria. We’re lucky that we have complementary strengths. Usually if one of us didn’t want to do something, or didn't know how, the other could handle it.”

"You have no idea if you’re going to succeed or fail, but there's only one way to find out."

Advice to other accounting professionals

Cloudsourced Accounting helps traditional accounting and bookkeeping professionals with their move to the cloud. Blake says that in order to reap the benefits of the cloud, accounting professionals must make a wholehearted commitment to it.

“You’re not going to be successful without full commitment – as with any major shift in a business,” he advises. “If you're a manufacturer, would you bring in new equipment and not train your employees on how to use it? Why would it be different with cloud accounting software? The benefits can be extraordinary.”

The unexpected benefits of moving to the cloud

In December 2014 Blake and Samantha welcomed their first son, Thomas. They were shocked to learn that Thomas was born deaf due to a genetic condition. When Thomas was one year old, he underwent surgery to receive cochlear implants, allowing him to hear for the first time.

Blake fondly remembers the first time his son reacted to sound. He also remembers the convenience of being able to work online while looking after Thomas.

“I remember sitting in the waiting room at UCLA, working on the wi-fi while Thomas was in surgery,” Blake says. “I went to every one of his appointments. Because I work on the cloud, I could be there for my son without having to sacrifice my business.”

Keeping the passion for music alive

Today, Blake continues to work hard while spending time with his family. Blake, Samantha and Thomas may soon relocate. “L.A. is very expensive. It’s not a great place to raise a kid. But because my work is virtual, we can go anywhere,” he says. “We could move up to Seattle where my parents live. Or we could go to a smaller town – we’ve always wanted to raise a family in a small town. As long as they have broadband internet, we’re good!” he laughs.

Although Blake’s life took a turn away from the cello and toward a career in accounting, his love for music hasn’t faded. He would one day like to start a chamber music group or be on the board of a symphony orchestra.

“I'm a musician at heart," Blake says. "I might have given up on music completely if I was working in an office somewhere – but thanks to the flexibility of the cloud, I don't have to."